Looking back at the many faces the King of Pop had throughout his career...

LOS ANGELES – Almost four years since Michael Jackson died from an overdose of the surgical anesthetic Propofol and other sedatives, the wrongful death lawsuit filed against concert promoter AEG Live by mother Katherine Jackson and the King of Pop’s three children has commenced.

Jackson died just two weeks before he was set to debut his highly-publicized “This is It” concert tour in London, and his family alleges that the concert promoters negligently hired and supervised former cardiologist Conrad Murray and breached its duty of proper care.

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However, many trial followers were shocked by the $40-42 billion figure reportedly put forward by the Jackson family as the entertainer's estimated earnings should he have not died at the age of 50.

But could Jackson really have been worth that much so long after his heyday of the 1980s and 90s?

“It seems they are throwing out this astronomical figure to try and win really big,” a source closely connected to the Jackson clan told FOX411’s Pop Tarts column. “The thinking is that while a jury probably wouldn’t award $40 billion or more, they could be led to believe that perhaps 10 percent of that, or $4 billion, would be reasonable.”

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At the time of his death, multiple reports indicated the star died with very little money and was beset with debt due to “Wacko Jacko” inspired spending habits and the fortune it took fighting accusations of child molestation.

“Not only that, but he hadn’t had a hit record in 20 years and he told everyone who would listen that he wasn’t interested in touring anymore and he only agreed to do the AEG tour because he was flat broke and out of options,” continued the source, adding that Jackson knew if he didn’t fulfill those contractual obligations he would be forced to forfeit his most prized possession: his share in the Beatles catalogue, estimated to be worth around $1 billion in 2009.

Another insider told us that Jackson was even living rent free in the Los Angeles home of his friend, fashion designer Christian Audigier, best known as the force behind Ed Hardy, when he died.

Audigier did not respond to a comment request.

“Michael had gotten lazy, he was never going to be worth $40 billion again,” insisted a source.

But where that figure even came from is up for some debate. An attorney for the Jackson’s told us that $40-42 billion was never listed on the complaint, and another lawyer for the family has said that they never asked for such a sum.

AEG attorney Marvin Putnam, who did not respond to a request for further comment, previously said the $40-42 billion in damages was indeed the amount put forward.

In compliance with California law regarding wrongful death cases, the plaintiffs submit evidence in support of a specified damage sum. But the actual amount awarded is determined by the court both the evidence submitted by the petitioner and defense. Wrongful death damages look at both economic damages – a fixed standard used to quantify the compensation for the loss of wages and benefits a decedent would have been able to provide in the future – and noneconomic damages, which requires no fixed standard to determine the value the loss of the decedent’s love, comfort and moral support.

And according to another attorney formerly connected to the famous family, the reported monetary amount is not too far-fetched.

“The issue is would it have been foreseeable of a man of Michael’s talent, legend and ability to perform (whether it be concerts, including recordings and merchandising) until the end of his life – life expectancy of a man is the late 80’s today,” said Debra Opri, former Jackson family attorney and leading entertainment lawyer. “Something I learned when I first entered the world of the celebrity performer, their income was beyond the average comprehension of an everyday earner.”

Opri pointed out that the “Thriller” sensation was already worth, through his songbooks of other recording artists, like the Beatles for example, in the multi millions.

“Yet the media was too busy speaking of his wild spending habits. However, if you were to look over his 25 years of recording history and where he was headed, sellouts of upcoming concerts in the millions of dollars within hours of going on sale, merchandising and earnings from his songs and other avenues of income… The anticipation was mutual and AEG was willingly advancing millions of dollars to MJ prior to the actual concert,” she continued. “No one throws money of that magnitude at a performer unless they are certain he will deliver. For a celebrity of MJ’s caliber, what is too much?”

Jackson’s two oldest children, Prince and Paris, are on the witness list to testify, along with singers Prince and Diana Ross, and his ex-wives Lisa-Marie Presley and Debbie Rowe.

And be warned – there may be no end in sight regarding the Jackson versus AEG war anytime soon.

“The 40 billion dollar number might seem arbitrary, but it’s safe to say that if the jury in this case finds that AEG Live is liable for the negligent hiring and supervision of Dr. Murray and that resulted in Michael’s death, the plaintiff’s attorneys will be ready with expert witnesses to prove that amount,” said California-based defense lawyer, David Wohl. “Don’t count on the jury actually awarding that much, and whatever they do award will result in an appeal by AEG, meaning this case could drag on for years.”